Luxury rentals in Chicago

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Top-rated luxury holiday rentals in Chicago

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Luxe

Flat in Gold Coast

4.88 out of 5 average rating, 8 reviews

Luxury Designer Penthouse|Private Deck|Gold Coast

NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. In a completely redeveloped luxury brownstone, your 3 bedroom/3 bathroom penthouse offers ultra high-end appliances, design, and finishes, with two private patios/decks (truly unique amenity in Chicago) and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between!

Luxe

Apartment in Uptown

5 out of 5 average rating, 4 reviews

Ultra Modern Luxury - New Construction 4 Bedrooms

New Listing! New Construction! Ultra modern 2500 SF+ Four Bedroom Duplex Condo in the heart of Chicago’s Uptown/ Edgewater neighborhood steps to Lake Michigan, Andersonville and tons of dining/shopping/nightlife options. Condo includes a private rooftop deck with patio seating, fire pit and loungers. Red line train is half a block away. Garage parking included. Concierge services available. Short term or longer term insurance clients or traveling executives welcome.

Luxe

Flat in The Loop

5 out of 5 average rating, 16 reviews

Luxury Downtown 4BR | Exclusive Design PH

Elevate your Chicago experience in this breathtaking, luxury penthouse. Imagine stepping onto your expansive private balcony, Nespresso in hand, and knowing every detail, from the CB2 furnishings to your dedicated virtual concierge, is designed for your seamless comfort. This is more than a stay; it's an immersion in refined urban living, designed for the discerning traveler who demands both luxury and convenience.